Reference of 51839-15-7,Some common heterocyclic compound, 51839-15-7, name is Dimethyl 5-iodoisophthalate, molecular formula is C10H9IO4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
A mixture of dimethyl 5-iodo-benzerte-1,3-dicarboxylate (9) (320 mg, 1.00 mmol), bis(pinacolato)diborane (10) (279 mg, 1.10 mmol), potassium acetate (294 mg, 3.00 mmol), PdCl2(dppf)* (24 mg, 0.03 mmol) and dried DMF (6 mL) was stirred at 80C for 2 h. The reaction mixture was cooled to the room temperature. Then, dimethyl 5-iodo-benzene-1,3-dicarboxylate (9) (640 mg, 2.00 mmol), PdCl2(dppf) (24 mg, 0.03) and CsF (456 mg, 3.0 mmol; dissolved in 2.5 mL of water) were added. The mixture was stirred at 80C overnight and afterwards extracted for four times with diethylether (4 x 25 mL). The organic layer was dried with MgSO4 and the solvent was removed in vacuum. The crude product was purified by column chromatography (silica gel, ethylacetate/hexane, 3:7 v/v). Yield 82 %. M.p. 214-215 C. 1H-NMR (400 MHz, CDCl3): delta= 4.00 (s, 12H), 8.51 (d, 4H, J = 1.5 Hz), 8.72 (d, 2H, J = 1.5 Hz). 13C-NMR (100 MHz, CDCl3): delta= 52.5, 130.2, 131.5, 132.3, 139.9, 165.9. Rf= 0.50 (silica gel, othylacetate/hexane, 3:7 v/v). MS-EI, m/z (%): 386 (75) [M+], 355 (100), 327 (15), 194 (10). *[1,1′-bis(diphenylphoshino)ferrocene]dichloropalladium(II)].
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Dimethyl 5-iodoisophthalate, its application will become more common.
Reference:
Patent; Technische Universitaet Carolo-Wilhelmina zu Braunschweig; EP1972338; (2008); A1;,
Iodide – Wikipedia,
Iodide – an overview | ScienceDirect Topics – ScienceDirect.com